The founding of Expedia within Microsoft was a rare moment in the tech ecosystem — one that gave rise to numerous tech startups over the years. You can now see traces of Expedia entrepreneurial DNA scattered throughout the startup ecosystem.

And many of those startups have been funded by the guy who started it all: Expedia founder Rich Barton. Let’s call these startups “Baby Bartons” — just as the first crop of entrepreneurs emerging from Microsoft were dubbed “Baby Bills” after legendary co-founder Bill Gates.

Barton, who left Expedia in 2003 and later co-founded Zillow, won the trust and respect of his former co-workers by repeatedly betting on them to take on big challenges.

Two of Barton’s former Expedia execs —Avvo CEO Mark Britton and Glassdoor CEO Robert Hohman, both of whom raised money from Barton — spoke at the Zillow Premier Agent Forum last month, highlighting the leadership characteristics that they learned from the tech executive.

The Expedia story began within Microsoft in the 90s when Barton pitched Bill Gates on spinning off the company. And it is a story all about talent.

“I needed to build a team inside of Microsoft, and Microsoft was hiring the smartest, the most motivated, the most interesting people in the world at that time,” said Barton.

Rich Barton, right, with Robert Hohman of Glassdoor

“I was able to attract to my team at Expedia the most adventurous of that lot because I had said to them that we were on a mission to build the largest seller of travel in the world and that one day we would strike out on our own and spin out of Microsoft to be our own publicly-traded company,” said Barton. “That was my dream, and I was able to attract great people.”

Off in the distance you need a mountaintop that you’re trying to scale. That’s what I think pulls you through the wall.

Barton looks for that think-big mentality in the entrepreneurs he backs.

“Off in the distance you need a mountaintop that you’re trying to scale. That’s what I think pulls you through the wall,” said Barton, who also serves as a venture partner at Benchmark and board member at Netflix. “What helps your team follow you though the wall is that on the other side of the wall there’s a mountaintop and we have a dream of standing on that mountain top and raising our hands in the air and saying we made the top. When the wall happens, or the storm, or the clouds and you can’t see it, well you know it’s there, and it pulls you through.”

Robert Hohman, Founder & CEO of Glassdoor

Glassdoor’s Robert Hohman remembered working in a role at Expedia that was far out of his comfort zone.

“Rich repeatedly had the courage to bet on people,” said Hohman. “To grow in your career you have to do something you haven’t done before because if you’ve already done it you’ve mastered it, that’s not growth. I was young and I was running parts of Expedia that I had no business running.”

Hohman took an unlikely path to becoming a CEO, originally starting as an engineer at Expedia. His fascination with what makes a team tick, along with a mentor who set up repeated growth opportunities are what drove him to found and lead Glassdoor.

“I was fascinated by what makes people want to follow other people through a wall. I felt it about you (Rich). I felt it about a few other leaders in my life, and I always was trying to figure why does that happen,” said Hohman. “Why when you pull some groups of people together will they follow you into battle? That’s probably what drew me to it, and I’ve studied it over the years.”

Those vulnerable moments are the times that actually make people want to follow you through the wall.

Vulnerability and admitting mistakes are also key to Hohman’s leadership style.

“Letting people know who you are. Having the courage to let them see you — warts and all. That’s the big one,” said Hohman. “A lot of people, especially when they start teams, and I did when I started a team, you think you’ve got to have all the answers and you think that it’s not okay to admit that you don’t know or that you’re wrong, you made a mistake. Those vulnerable moments are the times that actually make people want to follow you through the wall.”

Mark Britton, Founder & CEO of Avvo

For Mark Britton, the founder and CEO of Avvo, acknowledging and dealing with fear got him through some of the toughest times when he started the lawyer recommendation site.

“Nine days after we launched we were sued in a nationwide class action lawsuit. It was a little bit of the business plan, but it also had gotten completely out of control,” said Britton. “I was so burned out doing all this media, trying to keep up with these very media-savvy class action personal injury lawyers who were coming after us. I was so burned out, Rich comes over, and he said to me ‘If it’s not frightening, it’s not important.’ That is one of the best pieces of advice that I ever got.”

If it’s not frightening, it’s not important. That is one of the best pieces of advice that I ever got.

At Avvo, leading the team has meant that Britton has embraced the imperfection that comes with running a company.

“There’s this assumption that you’re building something that is perfect, and I think to the extent that you can help people understand that you’re building something that is a lot like life and fundamentally imperfect and that there are times where we are going to struggle, but we’re smart and we have this vision that Rich is talking about,” said Britton.

Britton was surprised by the transparency and directness of the Microsoft and Expedia culture, and has used that to form part of the culture at Avvo.

“People were so direct and saying exactly what was on their mind,” said Britton, who contrasted that with his experience at a law firm. “Once I calibrated for that, it dawned on me that this is kind of the life blood of this company.”

For Britton, that focus on transparency was one of the most important lessons he learned at Expedia.

“It’s the why that brings teams together. It’s the why that pulls you through the hard times. You need to construct for you, your business, and your team of people a reason for what you’re doing that is bigger and more important than just the 10X,” concluded Barton. “The 10X is fun and it gets you to think big, but really it’s about something more than that. Construct a mission that makes you feel good about what you do in your business.”

Kevin Lisota is a web developer, photographer, videographer and a former Microsoftie. See more of his photos or reach him on on Twitter or Instagram.